Phosphine → HCID 178424811, compound

HRID 925032Notes

Reaction equation

HRID 925032 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[NH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([Li])CCC.Cl[P:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.P>C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[N:17][P:24]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 24404PhosphineHCID 66180ChlorodiphenylphosphineHCID 178418339ButyllithiumHCID 178424804HCID 178424804, compound

Product 1

HCID 178424811HCID 178424811, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

N1-(2,6-dimethylphenyl)benzamidine (3.36 g, 15.0 mmol) was dissolved in 50 mL of diethylether and cooled to 0° C. Butyllithium (7.50 mL of 2.0 M solution in diethylether, 15.0 mmol) was added dropwise, producing a fluffy white suspended solid. The slurry was warmed to room temperature and stirred for 2 hours. Chlorodiphenylphosphine (2.69 mL, 15.0 mmol) was added slowly at room temperature. The suspended solid became finer and denser and the solution became slightly yellow upon complete addition of the phosphine. Stirring was continued for 1 hour. The solution was filtered to remove a small amount of white solid, presumably lithium chloride, and the solvent was removed in vacuo. The yellow foamy residue was suspended in 50 mL of pentane and stirred for 3 hours. Filtration and drying afforded 3.46 g (56%) of off-white solid.

Workup

  1. customproducing a fluffy
  2. temperatureThe slurry was warmed to room temperature
  3. stirringStirring
  4. waitwas continued for 1 hour
  5. filtrationThe solution was filtered
  6. customto remove a small amount of white solid, presumably lithium chloride
  7. customthe solvent was removed in vacuo
  8. stirringstirred for 3 hours
  9. filtrationFiltration
  10. customdrying

Sources & evidence

ORD record
ord-cabcf76d0b7c468783ca310ff578e6d1
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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